Compound of alpha-methyl-heptyl-hydro-cupreicine and process of making same



Patented Oct. 20, 1936 2,058,081

UNITED STATES PATENT OFFICE COMPOUND OF a-METHYL-HEPTYL-HY- DRO-CUPREICINE AND PROCESS OF MAKING SAME Fritz Johannessohn, Mannheim-Feudenheim, and Heinrich Thron, Mannheim-Waldhof, Germany, assignors to Bare Chemicals, Inc., Nepara Park, N. Y., a corporation of New York No Drawing. Application December 24, 1935, erial No. 56,078. In Germany December 28,

3 Claims. (Cl. 260-26) It has been found that the bactericidal power camphoric acid. If the compound is heated with of the camphoric salt of a-methyI-heptyLhydrQ- some conc. sulphuric acid, a smell of caprylic alcupreicine, the toxin of octyl-hydro-cupr'eine or, coho] becomes perceptible. as it will be called for short in the following, the 2 To 46 parts f a 10% Solution of hydro- 5 OCtYI- Y D considerably exceeds that chloric octyl-hydro-cupreicine in equal parts of 5 Of other salts Of the same basic substance. ater is added a solution of camphoric a njunonia, the other salts, such as the hydrochloric, boric or corresponding in t composition t parts of rhodanic octyl-hydro-cupreicine, kill bacteria as camphoric acid in 35 parts of water A mucous pneumococcus and staphylococcus in a solution of Solution results from which on heating on the 10 1116000 p 110 1320000, the Camphoric octyl-hydrowater bath the camphoric octyl-hydro-cupreicine 10 cupreicine does so even in a solution of 1240000. is Separated out in the form of yeuowish resin The obj ct of t present invention therewhile the ammonium chloride formed in the reo the preparation 0f the hitherto unknown action remains in the solution. The resin is puricamphoric octyl-hydro-cupreicine in a manner fled by dissolving in 5 parts of lukewarm water 15 used for the production of salts generally. Asan and furthe heating" the mm on the water 15 examp e, octy 0f the formula bath. The camphoric octyl-hydro-cupreicine is freed from the liquid, dried and powdered. It CH3 is free from chlorine. I Various changes may be made in the details OHT"(CH)5"CH OC C CH disclosed in the foregoing specification without H 0 5H CH2 departing from the invention or sacrificing the N CHPAIPCH advantages thereof. H I In the claims aflixed to this specification no selection of any particular modification of the in- 5 CH3 vention is intended to the exclusion of other d modifications thereof and the right to subsequentcan be combined direct with camphoric acid but 1y make claims to any modification not covered by one can also allow to interact salts of both comthese claims is expressly reserved pounds with each other, as for example the sul- We claim:

phuric or hydrochloric octyl-hydro-cupreicine with the barium or with the ammonium or silver salt of the camphoric acid respectively. In these reactions the campboflc. acid is added to the coloured powder, easily soluble in lukewarm umdo group (underhned m the formula) water, diflicultly soluble in boiling water, soluble Examples in alcohol, ether, acetone, chloroform, benzene,

(1) 424 parts of octyl'hydro'cupreioine 100 2 hi pi tlgfgi p r ggaring the camphoric salt parts of camphoric acid and 3000 parts of Water of wmethyl heptyl hydro cupreicine are heated to 50-60 C. until dissolved. The soluprising the addition of camphoric acid to the tion which is of neutral reaction, is then treated with active carbon, filtered and the filtrate evaplmldo group of the a methyl heptyl hydro 40 cupreicine. orated to dryness. The camphoric octyl-hydrom h 1 cupreicme of the formula 3. The process for preparing the ca p 0110 sa t V of the a-methyl-heptyl-hydro-cupreicine com- (C27H40O2N2)2-C8H14-(COOH)2 prising the addition of camphoric acid to the is obtained in the form of a brownish resin imidofgmup 9 amethyl'heptyl'hydm' and be ground to a 1ight brown cupreicme by interactlon of a salt of the a- It is easily soluble in lukewarm water but difficult y D y y p Wit a S lt of t e to dissolve in boiling water. It is soluble in 3,1- Camp acidcohol, ether, acetone, chloroform and benzene; in FRITZ J OHANNESSOI-IN.

benzine it is practically insoluble. It contains HEINRICH THRON. 50

80.9% of octyl-hydro-cupreicine and 19.1% of 1. A new composition of matter, the camphoric 30 salt of u-methyhheptyl-hydro-cupreicine of the formula (C27H40O2N2) 2.CsI-I14.(COOH)2 a slightly 

